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Open-ring cucurbituril column aromatic hydrocarbon double-main-body compound and preparation method and application thereof

A technology of cucurbituril and pillar aromatics, which is applied in the field of double-subject compounds of ring-opening cucurbituril pillar aromatics and its preparation, achieving the effects of good quality, easy manipulation and efficient operation

Active Publication Date: 2021-02-26
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005]However, there is no relevant research report on the use of pillar aromatics and open-ring cucurbituril double-body bonded compounds as transmembrane channel molecules for related research and application, in view of The double-body compound of ring-opened cucurbituril columnarene has two different cavities, so that the molecule has both the properties of columnarene and the performance of ring-opening cucurbituril. The double-body of open-ring cucurbituril columnarene forms a linear cavity, so Has strong application research in the field of molecular ion transmembrane transport

Method used

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  • Open-ring cucurbituril column aromatic hydrocarbon double-main-body compound and preparation method and application thereof
  • Open-ring cucurbituril column aromatic hydrocarbon double-main-body compound and preparation method and application thereof
  • Open-ring cucurbituril column aromatic hydrocarbon double-main-body compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: In this example, the ring-opened cucurbituril columnarene double-host compound and its preparation are as follows:

[0034]

[0035] where R is (CH 2 ) m SO 3 Na, where m=3, y=1, k=1, n=1;

[0036]During the preparation, take dicarboxylic acid columnarene (25.14mg, 0.03mmol) and halogen-modified open-ring cucurbituril (164.64mg, 0.12mmol) and dissolve them in 20mL of N,N-dimethylformamide solution, and then react Triethylamine (36.43mg, 0.36mmol) was added to the solution, and reacted at 60°C for 12h; after the reaction was completed and cooled to room temperature, the reaction solution was poured into methanol to produce a precipitate, filtered by suction, and the solid was dissolved in water, and placed in a dialysis bag ( MW=2000) for 48 hours of dialysis, after the dialysis, the dialysate in the dialysis bag was spin-dried, and dried under vacuum at 30°C to obtain the ring-opened cucurbituril columnarene compound, a white solid of 71.17 mg, yield: 7...

Embodiment 2

[0038] Example 2: In this example, the ring-opened cucurbituril columnarene double-host compound and its preparation are as follows:

[0039]

[0040] where R is (CH 2 ) m SO 3 Na, where m=3, y=1, k=1, n=2;

[0041] During the preparation, dicarboxylic acid pyrene (25.14mg, 0.03mmol) and halogen-modified open-ring cucurbituril (84.00mg, 0.06mmol) were dissolved in 20mL of tetrahydrofuran solution, and then sodium carbonate (19.08mg , 0.18mmol), reacted at 70°C for 18h, after the reaction was completed and cooled to room temperature, the reaction solution was poured into acetone to produce a precipitate, suction filtered, and the solid was dissolved in water, and then dialyzed in a dialysis bag (MW=2000) for 72h. After the dialysis is finished, the dialysate in the dialysis bag is spin-dried and dried under vacuum at 45° C. to obtain the split-ring cucurbituril columnarene double-host compound molecule 2 (see Figure II ), white solid 68.41 mg, yield: 66.08%.

Embodiment 3

[0042] Example 3: In this example, the ring-opened cucurbituril columnarene double-host compound and its preparation are as follows:

[0043]

[0044] where R is -(CH 2 ) x -OPO 3 K 2 , where x=2, y=1, k=1, n=1;

[0045] During the preparation, dicarboxylic acid cylarene (25.14mg, 0.03mmol) and open-ring cucurbituril (133.57mg, 0.09mmol) were dissolved in 20mL of dimethyl sulfoxide solution, and potassium carbonate (62.19 mg, 0.45mmol), reacted at 100°C for 36h; after the reaction was completed and cooled to room temperature, the reaction solution was poured into diethyl ether to produce a precipitate, filtered with suction, and the solid was dissolved in water and dialyzed in a dialysis bag (MW=2000) for 48h, and dialyzed After the end, the dialysate in the dialysis bag was spin-dried and dried under vacuum at 60° C. to obtain the ring-opened cucurbituril columnarene dual-host compound, 76.86 mg of white solid, yield: 70.26%.

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Abstract

The invention discloses an open-ring cucurbituril column aromatic hydrocarbon double-main-body compound and a preparation method thereof. According to the ring-opening cucurbituril column aromatic hydrocarbon double-main-body compound, haloalkane modified ring-opening cucurbituril reacts with carboxyl on carboxylic acid modified column aromatic hydrocarbon to form an ester bond, and the ester bondis linked into the double-main-body compound; compared with single open-ring cucurbituril and pillar arene, the open-ring cucurbituril column aromatic hydrocarbon double-main-body compound has two cavities with different properties, one cavity is a pillar arene cavity, the other cavity is an open-loop cucurbituril cavity, the two cavities are arranged in a linear structure, and the cavities of the carrier have different properties. The compound has the properties of both pillar arene and open-ring cucurbituril, has very good molecular recognition capability, can be used as a molecular ion transmembrane transport molecule, and is applied to the industries of biomedical research, pharmacy, food, essence and flavor, tobacco and the like.

Description

technical field [0001] The invention belongs to the fields of chemical synthesis and preparation of new materials, and in particular relates to a class of split-ring cucurbituril columnarene double-body compounds and a preparation method and application thereof. Background technique [0002] Supramolecular chemistry is a discipline that studies the intermolecular recognition and self-assembly of two or more molecules through non-covalent interactions to form complex and ordered molecular aggregation systems. Among them, the recognition and self-assembly between supramolecular host molecules and other molecules is the main content of supramolecular research. Among them, macrocycles are the main supramolecular hosts. Common supramolecular hosts include crown ethers, cyclodextrins, cucurbiturils, pillararenes, and calixarenes; most of these host molecules have hydrophobic cavities that can be used to encapsulate small molecules to form host-guest systems, and are used in pharm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07F9/6561G01N21/64
CPCC07D519/00C07F9/6561G01N21/6428G01N2021/6432
Inventor 杨波孔令广朱盼永杜刚陈丽媛赵榆林廖霞俐杨靖
Owner KUNMING UNIV OF SCI & TECH
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